


Date Night

by WorldOfDemons



Category: Supernatural
Genre: Date Night, F/M, Fluffy, Gen, Smut, slightly insecure reader
Language: English
Status: Completed
Published: 2016-01-10
Updated: 2016-01-10
Packaged: 2018-05-12 22:16:20
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,055
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5682787
Author URL: https://archiveofourown.org/users/WorldOfDemons/pseuds/WorldOfDemons
Summary: <blockquote class="userstuff">
              <p>You and Dean go out for a date.</p>
            </blockquote>





	Date Night

You had never shied away from sex. Granted, you didn’t have quite as much experience as Dean, but you had taken your fair share of guys home from the bar. That had all ended for both of you when Dean was thrown against the wall by a werewolf and knocked out cold. In your defense, you honestly thought he was dead. If you had known he was alive, you wouldn’t have sobbed over his body and confessed your undying love for him. He found it amusing afterward. You did not. But it did act as a kick-start for your relationship. You had been dating for around 6 months; Dean wanted to take your relationship slowly.   
_“Every relationship I’ve ever been in turned out… not what I wanted to be. This is going to be different,”_ he told you. You dated properly, which was hard in the hunting life, but Dean was a romantic at heart. Below his hard exterior, he was a softy. Everything from dates and flowers, he had swept you off your feet. You were waiting for the topic of sex to come up. Your relationship was easy; you were comfortable. And even though you knew sex was coming, but that didn’t mean you were ready.

You were in Atlanta when Dean decided to take you out for a date night. You had made reservations for a restaurant, but just three hours before Sam caught a break in the hunt. You took care of the werewolf quickly. Sam had actually taken most the beating, being thrown against the wall while you managed to squeeze off the shot to the wolf’s chest. Dean all but sped back to the motel to drop Sam off in his room. As soon as Sam got out of the shower, Dean jumped in leaving you in the room next door. You only had about an hour and a half to get ready and get to the restaurant, which really wasn’t much time considering Atlanta traffic. You showered quickly and managed to shave your legs without butchering yourself, but you were running out of time. You jumped out of the shower and dried off before running the motel’s hairdryer over your hair and slipping into your dress. The little makeup you had was applied quickly and you were slipping on your heels on when Dean knocked on the door. When you opened the door. He stood leaning calmly against the doorjamb. He let out a low whistle.

“Damn, Y/N, you clean up nice,” you grinned at him.

“Not bad yourself, Winchester.” He was wearing his usual FBI suit but had somehow gotten a new tie, a dark emerald green, which made his eyes sparkle and pop. He glanced at his watch.

“We gotta go if we want to get to this place on time,” You nodded and followed Dean to the car. His fingers drummed on the steering wheel as he maneuvered through the traffic. His hand eventually made its way to your thigh, his fingers sneaking under the fabric.

“What’s so special about this place again?” He asked, his thumb rubbing small circles on your skin.

“It spins,” You answered grinning. He looked over at you as he pulled up to a stoplight.

“What?” You laughed at him.

“You’ll see when we get there,” You said as he pulled up to the hotel. You led him across the hotel floor and over to a desk.

“Reservation for Winchester,” You told the woman behind the desk. She checked her list before smiling up at you.

“You can go ahead to the elevator,” She said gesturing behind her. You could feel Dean’s confusion, but he didn’t say anything. He was like a kid as the glass elevator took you up to the top of the building. As soon as you stepped off, a waiter took you to your table right next to a window. Dean watched the skyline in awe before looking back to you.

“We’re moving? We’re actually spinning?” You pointed to a building.

“Watch for a second,” You said while you looked over the menu. You already knew Dean would order the steak and you settled on a roasted duck breast.

“This is amazing,” Dean muttered. You set the menu down and looked up at him. He reached across the table and took your hand.

“This is really amazing,” He told you, his green eyes sparkling.

“I figured you’d like it. Figured you’d like the NY Strip, just so you don’t have to bother with all the fancy terms you were so worried about.” Dean broke out into a grin.

“You know me so well,” He said laughing gently. You just shrugged and smiled at him.

“I think I’m supposed to.” The waiter came and took your orders and recommended a wine, which he quickly brought for you and Dean. You relaxed with Dean slipping into easy conversation about anything but hunting and your normal lives. You talked about everything from your family before to Dean telling embarrassing stories about him and Sam, but mostly Sam. Dinner came and went as the sun dipped below the skyline and the city lights started to glow. You split a dessert and sat just enjoying each other.

“Sam’s probably asleep by now,” Dean commented offhandedly. You hummed slightly in response. He stood slowly and held your hand tightly as he led the way out of the restaurant. The night was crisp as you walked to the car hand in hand.   
You leaned against the passenger door of the Impala while Dean pressed his body along yours, kissing you deeply. It started gently but quickly became more heated. His fingers dug into your waist until you finally broke away.

“Motel?” You asked breathlessly. Dean nodded, lust darkening his eyes. He drove as quickly as the traffic would allow him until he made it to the motel. Dean couldn’t keep his hands to himself the entire drive, his fingers skimming over your inner thigh. As soon as the car was shut off, you instantly climbed into his lap, your lips attacking his. Your skirt was pushed up around your waist as you straddled him. His hands came around your waist as you ground down on him and you felt him getting hard under you.

“Into the room,” He groaned. You climbed out of the driver’s side first, Dean following close behind you. He fumbled with the key for a second before pushing you into the room. As soon as the door was closed, Dean pushed you against it. His arms wrapped around under you ass; he picked you up and your legs wrapped around his waist. He held onto you as he walked over to the bed and set you down to stand in front of him. He turned you around gently and pulled the zipper down your back. His fingers gently brushed your skin making you shiver slightly. He pushed the dress off your shoulders making it pool at your feet leaving you only in your lacy black bra and matching panties. He unhooked your bra and let it join your dress on the floor. You turned around as he shrugged off his jacket and started loosening his tie. He pulled it over his head while you started on the buttons of his shirt. One by one, you popped them slowly, Dean’s hands coming to rest on your waist. He helped you push his dress shirt off his shoulders and he tossed it across the room. You dropped to your knees and undid the button of his dress pants. He carefully stepped out of them and you palmed his member through the thin cloth of his boxers. You glanced up at him as you tugged at the waistband. His breathing hitched as you pulled down quickly. You wrapped your hand around the base and gave him a few slow strokes.

“Shit, Y/N,” he breathed. You looked up at him and made eye contact with him as you took him into his mouth. Your eyes closed as you took him further into your mouth until he hit the back of your throat. Your head started bobbing quickly; his hands rested in your hair, not enough to take control, he just needed something to hold onto. You hollowed out your cheeks and sucked hard. Dean groaned before pulling you off of him and pulling you up onto the bed. He practically jumped on you and kissed you hard.

“If I didn’t make you stop,” he muttered against your lips, “I would’ve come so hard, and I don’t want that.” He broke away and started kissing down your body, gently nipping at your breasts before kissing your stomach and settling between your legs. His fingers hovered around the waistband of your panties. Realization dawned over you and you grabbed his hands. He looked up at your surprised.

“I’m sorry, Dean. I…” you blushed slightly. He sat up and looked at you.

“Y/N, if you don’t want to do this, it’s fine.” He comforted. You shook your head.

“It’s not that, I was just in a rush to get ready and didn’t exactly,” you hesitated slightly, Dean waiting patiently for you to finish.

“I didn’t take care of anything _down there_ if know what I mean.” Relief flooded his face.

“Is that all?” He asked smiling.

“Y/N, you’re beautiful no matter what. You’re just as gorgeous dressed up in that restaurant as you were shooting that wolf earlier. Nothing is going to change that for me. You are beautiful, strong, passionate about everything, so I don’t care. I want to be with you – if you’ll have me.” You smiled gently and nodded. Dean smiled.

“In that case, I’m going to make you feel so good, sweetheart, you’re going to forget your own name,” Dean smirked as he hooked his fingers into the waistband of your panties and pulled down quickly. He carefully pulled your legs apart and kissed the inside of your thighs. You squirmed slightly as his tongue pushed into you.

“Dean,” you gasped your hands twisting into his hair. He knew exactly what he was doing as he pulled pleasure out of you. His lips closed around your clit making you whine and buck against him. His hand spread across your hip, holding you down. You inched closer and closer until you were coming hard. When you came back, Dean was watching you smiling.

“So hot when you come, ya know that?” You shook your head slightly.

“You are,” he confirmed crawling up your body and pressing a chaste kiss to your lips. You wrapped your hand around his head and pulled him closer to you. Your knees came up around his waist opening you up to him. His hand came up under your knee as the head of his cock pressed into you. Gently he pushed fully into you, his body fitting exactly with yours. He was careful with you, as he started moving. His cock filled you perfectly and with every push he brought you closer and closer to coming. He moved faster setting a steady rhythm. You started moving with him, your hips rising to meet his with every thrust. His hand slipped between your bodies and gently rubbed your clit. Your legs wrapped around his waist, making him hit even deeper.

“Dean,” you gasped, “I’m going to come,”

“Me too,” he grunted. He increased the pressure on your clit just a bit more and you were coming again, this time, Dean came with you. You held on to him as you both caught your breath. He eventually rolled off of you and went into the bathroom bringing back a wet washcloth. You let him clean you up before grabbing one of his old shirts and a pair of panties before climbing back into the bed. Dean slipped on a pair of pajama pants before lying down and you curled up against his chest.

“So date night? I think I like this.” He murmured to you while he ran his fingers through your hair.

“I mean, awesome food, mind-blowing sex, absolutely beautiful girl about to fall asleep in my arms? Sign me up.” You laughed slightly but didn’t answer as his breathing evened out and you both drifted to sleep. Date night was definitely around to stay. 


End file.
